1-Pentyne → Ethyl (3-(pentyne-1-yl)phenyl)acetate

HRID 59021

反応式

HRID 59021 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:33]#[C:34][CH2:35][CH2:36][CH3:37]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:33]([C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:11]=[CH:10][CH:9]=1)#[C:34][CH2:35][CH2:36][CH3:37]

参加物

6

反応物 3

HCID 123091-PentyneHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

生成物 1

HCID 67100180Ethyl (3-(pentyne-1-yl)phenyl)acetate収率 80.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of ethyl(3-bromophenyl)acetate (0.3 g, 1.24 mmol) and tetrabutylammonium fluoride hydrate (0.97 g, 3.72 mmol), was treated with PdCl2(PPh3)2 (26 mg, 0.037 mmol; 3 mole %) and 1-pentyne (367 μL, 3.72 mmol) in a sealed tube. The tube was heated at 80° C. for 2 h. The mixture was treated with water, and was extracted with diethyl ether. The organic extract was dried over sodium sulfate, filtered and evaporated in vacuo to give the crude product. Purification on a Biotage™ 25 M column (silica), eluting with ethyl acetate/hexane 0:1 to 2:98, gave ethyl (3-(pentyne-1-yl)phenyl)acetate as a pale yellow oil (0.23 g, 79%).

後処理

  1. extractionwas extracted with diethyl ether
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customPurification on a Biotage™ 25 M column (silica)
  8. washeluting with ethyl acetate/hexane 0:1 to 2:98

出典と根拠

ORDレコード
ord-88dbc1b4edb54ade9774a49832ce807e
出典データセット
uspto-grants-2016_09
特許番号
US09439882B2

関連ノート

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